Multi-step reaction with 14 steps
2.1: sec-butyllithium / tetrahydrofuran / -78 °C
2.2: 32 percent / tetrahydrofuran / -78 °C
3.1: 29 percent / TiCl4; triphenylphosphine / CH2Cl2 / -78 - 0 °C
4.1: 95 percent / 2,6-lutidine / CH2Cl2 / 0.5 h / 0 °C
5.1: N-methylmorpholine N-oxide; OsO4 / H2O; 2-methyl-propan-2-ol; various solvent(s) / 20 °C
6.1: lead tetraacetate / benzene / 0.5 h / 20 °C
7.1: 2.778 g / tetrahydrofuran; diethyl ether / -78 - 0 °C
8.1: 94 percent / oxalyl chloride; dimethyl sulfoxide; triethylamine / CH2Cl2 / -78 - 20 °C
9.1: lithium diisopropylamide / tetrahydrofuran; hexane / 0.33 h / -78 °C
9.2: tetrahydrofuran; hexane / 0.33 h / -78 °C
10.1: N-bromosuccinimide / tetrahydrofuran / 0.75 h / 0 °C
11.1: 101.0 mg / camphorsulfonic acid / CH2Cl2; methanol / 0 - 20 °C
12.1: triethylamine; sulfur trioxide-pyridine complex / CH2Cl2; dimethylsulfoxide / 0.67 h / 0 °C
13.1: SmI2 / tetrahydrofuran / 0.75 h / -78 °C
13.2: 4-(dimethylamino)pyridine / tetrahydrofuran / 0.5 h / 0 °C
14.1: 389.8 mg / sodium borohydride / CH2Cl2; methanol / 0.17 h / 0 °C
With
2,6-dimethylpyridine; lead(IV) acetate; sodium tetrahydroborate; N-Bromosuccinimide; osmium(VIII) oxide; samarium diiodide; oxalyl dichloride; camphor-10-sulfonic acid; sec.-butyllithium; sulfur trioxide pyridine complex; titanium tetrachloride; dimethyl sulfoxide; 4-methylmorpholine N-oxide; triethylamine; triphenylphosphine; lithium diisopropyl amide;
In
tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; dimethyl sulfoxide; tert-butyl alcohol; benzene;
2.1: Metallation / 2.2: allylsilylation / 3.1: Cyclization / 4.1: Etherification / 5.1: Oxidation / 6.1: Oxidation / 7.1: Addition / 8.1: Oxidation / 9.1: Metallation / 9.2: Etherification / 10.1: Bromination / 11.1: Hydrolysis / 12.1: Oxidation / 13.1: Cyclization / 13.2: Acetylation / 14.1: Reduction;
DOI:10.1021/jo990989b